Sodium hydride → Ethyl 4-chloro-1-methyl-6-(2-nitrophenoxy)-2-indolecarboxylate

HRID 565040노트

반응식

HRID 565040 반응식
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12].[H-].[Na+].F[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28]>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N+:27]([O-:29])=[O:28])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 21194263Ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate

생성물 1

HCID 21194137Ethyl 4-chloro-1-methyl-6-(2-nitrophenoxy)-2-indolecarboxylate수율 94.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

After 0.42 g (1.64 mmol) of ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate was added to a suspension of 0.066 g (1.64 mmol) of 60% sodium hydride and 5 ml of dimethylformamide, the suspension was stirred at room temperature until the mixture became an almost transparent solution. Then 0.35 g (2.49 mmol) of 1-fluoro-2-nitrobenzene was added to the solution at room temperature followed by stirring for 5 hours at the same temperature. The reaction mixture was poured onto ice water. The resulting mixture was then extracted three times with ethyl acetate. The combined extracts were washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was isolated and purified by silica gel column chromatography to give 0.53 g (94.3%) of ethyl 4-chloro-1-methyl-6-(2-nitrophenoxy)-2-indolecarboxylate.

후처리

  1. stirringby stirring for 5 hours at the same temperature
  2. additionThe reaction mixture was poured onto ice water
  3. extractionThe resulting mixture was then extracted three times with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was isolated
  8. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-bb4a6048ed284f78a01b609b5489867d
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06169107A

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